So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Gannedi, Veeranjaneyulu; Villuri, Bharath Kumar; Reddy, Sivakumar N.; Ku, Chiao-Chu; Wong, Chi-Huey; Hung, Shang-Cheng researched the compound: 2,3-Dibromo-1-propanol( cas:96-13-9 ).SDS of cas: 96-13-9.They published the article 《Practical remdesivir synthesis through one-pot organocatalyzed asymmetric (S)-P-phosphoramidation》 about this compound( cas:96-13-9 ) in Journal of Organic Chemistry. Keywords: covid19 remdesivir organocat remdesivir synthesis nucleotide; organocatalyst stereoselective phosphoramidation coupling synthesis remdesivir anticoronavirus crystal structure. We’ll tell you more about this compound (cas:96-13-9).
Remdesivir, an inhibitor of RNA-dependent RNA polymerase developed by Gilead Sciences, has been used for the treatment of COVID-19. The synthesis of remdesivir is, however, challenging, and the overall cost is relatively high. Particularly, the stereoselective assembly of the P-chirogenic center requires recrystallization of a 1:1 isomeric p-nitrophenylphosphoramidate mixture several times to obtain the desired diastereoisomer (39%) for further coupling with the D-ribose-derived 5-alc. To address this problem, a variety of chiral bicyclic imidazoles were synthesized as organocatalysts, e.g. I, for stereoselective (S)-P-phosphoramidation employing a 1:1 diastereomeric mixture of phosphoramidoyl chloridates as the coupling reagent to avoid a waste of the other diastereomer. Through a systematic study of different catalysts at different temperatures and concentrations, a mixture of the (S)- and (R)-P-phosphoramidates was obtained in 97% yield with a 96.1/3.9 ratio when 20 mol % of the chiral imidazole-cinnamaldehyde-derived carbamate was utilized in the reaction at -20°C. A 10-g scale one-pot synthesis via a combination of (S)-P-phosphoramidation and protecting group removal followed by one-step recrystallization gave remdesivir in 70% yield and 99.3/0.7 d.r. The organocatalyst was recovered in 83% yield for reuse, and similar results were obtained. This one-pot process offers an excellent opportunity for industrial production of remdesivir.
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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem